Where to start a successful collaboration with a freelancer? By reading this guide!

Hiring a freelancer or a contractor to help with communications and content leads too often to dissatisfaction. 

I’ve seen the challenges of hiring help from both sides of the table. First, as a journalist and project manager collaborating with writers, photographers, designers and more; later, as a freelance copywriter creating content for ambitious businesses and projects with a story to tell.

When you look at the equation, it is quite a complex one: Finding the right fit is a mix of style, talent, experience, strategy, timing and personal chemistry – all this in a field where personal taste and preferences play a big role.

Thus, I distilled my knowledge and experience from both sides of the table into this outsourcing guide, to help small teams of ambitious one-person brands to groups of communications professionals in order to hire help better. Because I know from my own experience that content collaborations can be enjoyable and create results.

The best part: it all boils down to five questions!

1 – Is this the right project to entrust someone outside the team?

Surprisingly, the first question in the process of hiring help is not “Does someone know a good freelancer?”. Instead, it’s some form of the question “Should we be doing this right now?” 

The first step to successful outsourcing is understanding which projects can easily be entrusted to a person outside the team and when is the right time to keep the business in-house. This applies to communications professionals in bigger organisations and one-person-wonders alike.

Still on the fence about whether now is the right time to ask for help? Read the previous article on making smarter outsourcing decisions fast and download the handy map for future decision-making below!

2 – What are our goals and how do we measure them?

A goal can be something as simple as saving your own time or something as ambitious as doubling website traffic or tripling conversion rate. Whatever it is, ensure it’s clear for everyone involved and that it can be measured in numbers. 

If your goal is to save time within the team, have everyone involved in the project track the time they spent on the project. If the end goal is to improve reach, engagement or conversion, be sure to have the baseline information ready before doing anything else. 

What’s annoying about this question is that it can reveal the need for a strategy update. As annoying as that is, you’ll be happy to have realised that before investing a part of your marketing budget on a project that wouldn’t have taken you and your team closer to the end goal anyway. 

It’s sometimes even happened to me to talk a potential client out of their idea to hire me to write content for them. Instead, we’ve embarked on a strategy collaboration that maybe lasted longer – but so did the results they achieved. But that’s a story for another day!

3 – Do we need help on the whole project or a smaller part?

Are we still not calling that star freelancer everyone raves about? Not quite yet.

After clarifying the right moment to move forward as well as the goals of the operation, it’s often helpful to review whether the whole project is worth outsourcing or not. Sometimes all that’s needed is a specialised part that’s hard to produce in-house, like a video or animation.

Breaking the project into smaller chunks is also a viable strategy when working with freelancers who are new to your brand. It allows you to get acquainted with your extended team members and their special talents before launching a bigger collaboration.

 4 – How are we going to work together?

Now we’re finally approaching the phase where the phone call or email can go out, as it’s time to talk about the process!

This step is all about how the collaboration with an external contributor will go. Who will be in charge of briefing the freelancer? Which pieces of information do they need? How much time will be needed for each step?

It’s a good idea to include the collaborator you’re planning to work on in this discussion. Seasoned freelancers have experience on the best ways to run a project and they can guide you through potential pitfalls and also explain their own process.

If this question makes you squirm and think to yourself that you don’t even know which steps the process should include, make figuring that out your priority project first. Hop back to step one to decide whether you’d like to hire someone from the outside to do the process mapping for you!

5 – How and when is feedback delivered?

When talking about the process, one question is particularly important and deserves its own paragraph. How are you going to deliver feedback to your freelancer, and when do these feedback rounds take place?

In bigger organisations, it’s also worth thinking about who needs to validate the work and at which moments will these validations happen. 

Giving constructive feedback is an inescapable part of working with people outside your business or team. Even when working with the most talented people, you are likely to face the indescribable feeling of “Nah”.

More articulate people tend to say “This is clearly high-quality work but not exactly what we were looking for.” (That’s how you recognise an experienced outsourcer!)

To avoid those “Nah” moments from lingering on longer than usual, brace yourself to give detailed feedback often, especially at the beginning of a new collaboration. Only tireless feedback will help freelancers find the tone of voice and visual style of your brand.

+ What did we learn from this that could be implemented in future projects?

Aren’t we at the end, yet? Almost! With the first five questions, you’re already well-equipped to brief a freelancer for success. 

However, once the project is finished, there is one more important question to ask: What can we learn from this experience?

Continuous improvement and reflection, ideally together with the in-house team and freelancers, aimed at fine-tuning the process so that it is seamless. That is the secret ingredient that makes collaboration fruitful and fun for both the contracting team and the lucky freelancer who has an opportunity to work with them. 

Are you missing out on freelancer magic?

Have you found that magic formula and freelancer with whom work feels like a hobby?

If not, I’d love to hop on a call and talk about how you could get help and move your amazing plans forward. In the meantime, download your Content Outsourcing Map below!

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